Trifluoroacetic acid → HCID 57966240, compound

HRID 420609Notes

Reaction equation

HRID 420609 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:17]=3[N:18]=2)[C@H:10]([CH2:27][O:28][CH3:29])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:29][O:28][CH2:27][C@@H:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[C:14]1[S:15][C:16]2[CH:22]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66657855HCID 66657855, compound

Product 1

HCID 57966240HCID 57966240, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-methoxymethyl-4-(6-trifluoromethyl benzothiazole-2-yl)piperazine-1-carboxylic acid t-butyl ester (167 mg) in methylene chloride (1.5 mL) was added trifluoroacetic acid (0.3 mL). The mixture was stirred at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure. Saturated aqueous sodium hydrogencarbonate solution was added thereto and extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the title compound (123 mg). Yield: 96%.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogencarbonate solution was added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-987385272cbe4920bba20bae725bac6a
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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